Hydrochloric Acid → HCID 89462946, compound

HRID 1525320Notes

Reaction equation

HRID 1525320 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:17]C(=O)C)([CH3:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH2:17])([CH3:15])[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89462671HCID 89462671, compound

Product 1

HCID 89462946HCID 89462946, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of compound 33-e (5 g, 15 mmol) in H2O (25 ml) was added concentrated HCl (12.3 ml, 150 mmol). The reaction mixture was then refluxed for 60 hours. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate. The water phase was adjusted to a pH of about 8-10 by aqueous NaOH (2N), then extracted with ethyl acetate and washed with brine, dried and concentrated to give 2-(6-(4-bromophenyl)pyridin-3-yl)propan-2-amine (2.6 g, 59%).

Workup

  1. temperatureThe reaction mixture was then refluxed for 60 hours
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13288429a0414c0383167b695cd7399c
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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